Sister Cheryl Wint, OSF, Transformation Includes Looking at the Next Generation

Sister Cheryl Wint, OSF is a fountain of knowledge and infectious enthusiasm for God’s work. Everything she shares is a nugget of wisdom that leaves you wanting to know what she will say next.

As a board member of St. Francis Healthcare System, her whole-hearted dedication to the mission shines brightly. Her conversations are not filled with romanticized notions but only a genuine devotion to fostering the movement of God in the hearts of people, Church and society. Rooted in foundation yet with a progressive eye, Sister Cheryl admits being uncomfortable with the term “treasures” in reference to the Sisters because it does not capture the spirit of Franciscan Sisters in the future.

Challenges Parallel to Religious Communities
Sister Cheryl recognizes that St. Francis Healthcare System is in a state of transformation and that some employees, especially those who have been with the organization for a long time, may be uncomfortable with the current transitional state.

She hones in on the issue of change at St. Francis Healthcare System and approaches it philosophically. In addition, she draws parallels to the challenges facing religious communities, especially the merged Sisters of St. Francis of the Neumann Communities as well as the Church overall.

According to Sister Cheryl, the younger (ones 65 and younger) Sisters of St. Francis get together twice a year to engage in a contemplative process about the future. The Sisters’ initial approach to this process was “business as usual” and strategic planning routine where everyone knows what to expect and how to execute. However, at recent “futuring” sessions, there was a twist.
The facilitator lifted the Sisters out of their comfort zone and challenged them in new ways. It was not business as usual this time.

“For the first couple of meetings, I was frustrated,” admits Sister Cheryl, who was previously immersed in the business world serving as a vice president of a tech company before becoming a Sister who now successfully merges that mindset with the healthcare ministry. “I wanted to say, ‘Let’s go on with it.’ It was tough because we were so used to the other way of doing things.”

Focusing on Our Strengths
The usual process which involves developing a strategic plan, rolling up our sleeves and getting on with it went out the window at this meeting. Instead, they were challenged to know each other, to really know each other to the point where one would know what each other likes in their coffee. This would come before the process of developing a plan for the future. It was a welcomed wake-up call.

Contemplative Dialogue
At this meeting, the concept of contemplative dialogue was introduced to the Sisters. It’s a process that engages minds and hearts in a new way. It involves silence and listening for reflection and deeper conversation. It suspends debate and mere problem-solving to allow for creative possibilities, emerging options, and peaceful resolution. Ultimately, with this contemplative approach, any group conversation can become a spiritual experience instead of just a business meeting.

The premise was simple but profound. The group could not possibly talk and plan, or shape the future of the Sisters of St. Francis without first knowing each others’ strengths. They were encouraged to not simply go through the motions, but to be more reflective in prayer, listening and dialogue together. Utilizing moral leadership, they are to collectively know and answer “What they are steering into the future? What will they need to do so?” Sister Cheryl believes these same processes could be applied to St. Francis Healthcare System and the Church.

Church Eras
Historically, the Church has undergone change, with distinct eras characterized by specific principles, which have lasted for 300 years. The Church’s last era, the Apostolic Era, lasted from 1500 to 1800, and our current Mission Era, started in 1800 and will continue through 2100.

“Initially, you see a rise in the first two-thirds of the era, and by the last third, there is a decline, which sets the stage for the next era,” Sister Cheryl explained.

“The current generation are the builders and doers, with partnerships and collaborations. St. Francis Healthcare System is already there,” Sister Cheryl said. “In the next generation we will see more individuals with creative and imaginative gifts.”

Engaging the Next Generation
Sister Cheryl believes that as St. Francis Healthcare System continues to build its Liliha complex, it should also be creating a culture to engage the next generation so that they are ready to operate that complex. “They are the ones inheriting this and making the decisions for their parents…Our message to them must be: ‘We are helping you live the life you were called to live in peace, knowing that your Mom and Dad are in good hands.’”

Sister Cheryl said this requires holistic planning and a commitment to transformation versus change.

“Change is something you do with your socks. Transformation is much more complete, like how a caterpillar changes to a butterfly. Butterflies have a different brain and a completely different digestive system that depends on nectar instead of leaves. That’s a total transformation of being. The in between phase, called the chrysalis in the life of a caterpillar, this is where all the work really takes place and that effort and juice is not wasted it is part of the foundation. We too are called to deconstruct ourselves as we enter into the future. Our commitment to the work it takes to transform determines what kind of future we will envision and leave behind for others to live.”

An example of this kind of preparatory transformation is already under way with the next generation. Sister Cheryl is excited about the way the youth of today are living out their commitment to service especially in performing arts classes. They not only do moving plays and creative writing on the saints from a different perspective to tell their stories, they are also living this out in doing palliative care service projects as a new class curriculum and using drama as a way of passing this on to the next group of classmates.

“It’s their interpretation of what it must be like,” Sister Cheryl said. “It starts with a retreat at Kalaupapa for the teachers, who then are inspired to take their 12th graders on a retreat, then it becomes integrated into the curriculum for schools throughout the state.

The results are “sacred performances” that generate inquiries from Catholic Schools to public charter schools.

The Need for Patience and Faithfulness
As St. Francis develops the St. Francis Kupuna Village, there may be a tendency to grow impatient with our progress. Sister Cheryl looked to Hawaii’s two saints as models, pointing out their differences in style.

“Damien’s virtue for example was a ‘rugged perseverance’ approach. Marianne’s was divine patience, which is how I need to be,” Sister Cheryl added. “Marianne wanted to go to Molokai, but was initially prohibited from going there. She could have gone back to New York. She was not perturbed by the delay, and instead of bemoaning that it was taking so long for her to go, she ended up building schools, orphanages and healthcare facilities.” This included a hospice program which back then was one of the first of its kind. This was the forerunner that eventually made Hawaii known for having one of the top five hospice facilities in the nation.

“In the waiting, we can ask ourselves, ‘What is God calling us to and how can we develop and strengthen ourselves to better serve God’s people?”

As in the parable of the talents, Sister Cheryl said we should not be like the servant who buries his talent in the ground, but should invest it properly for better returns. So let our mana‘o count and our aloha continue to be exceptional.

Mahalo nui loa for all that you do so that Spirit-led we journey into the future.